Are you an SDR who feels stuck in a rut? Do you have a clear picture of your sales career goals? Are you working towards becoming an AE, but continually finding it just beyond your reach? Do you feel like your career progression has hit the wall?

In this episode of INSIDE Inside Sales, Darryl speaks with Scott Ingram, the Founder of Sales Success Media and Director at Relationship One. Darryl and Scott talk about the importance of having a clear and concise career progression path, and offer tips on how to reach your career goals. They also offer up tips on getting clear communication from your employer, as well as steps to owning your development and knowing your options. Learn ways you can advance in your organization, right here on this episode of INSIDE Inside Sales!

Not in the mood to listen? No problem, you can read the transcriptions below.

Host:  Darryl PraillVanillaSoft

Guest:  Scott Ingram,

Is the SDR Role a Dead End?

Darryl Praill: How are you doing folks? It’s another week here, it goes by fast, doesn’t it? I say that every week. You must be getting tired of me saying that to you nonstop. I do apologize. What are you up to this week? Are you getting crazy, busy? Myself, I’m in back to back it seems, nonstop sales kickoff meetings. It’s the start of the year and we’ve got everybody flowing in from all around the world and we’re just getting our numbers ready and our assumptions. And it’s interesting, right?

Darryl Praill: Because VanillaSoft is a high-tech SaaS company, not a services company and that has context because part of the assumptions we make are there’s sales assumptions, there’s marketing assumptions and then there’s product assumptions, right? And as a sales rep you get it because you understand that while you’re going say, “Well I can control sales because that’s what I do.” I get it, I’m a rock star at what I do, that’s my thing, I got it.

Darryl Praill: But you know what? I really depend on marketing to generate a certain volume of leads for me. They got to build our brand up, they got to get us more engaged, they have to get us more visible, more aware.

Darryl Praill: So, if they don’t do that, my job sucks or you’re going to say, “I need the product team to make sure “we’ve got certain features and functions “because I can’t compete with my competition “because they have those functions “and we don’t have those functions, “and how am I supposed to compete?” I’m the bomb when it comes actually selling, but at the end of the day if they want feature A, B and C and I don’t have it, I’m dead in the water and you’re killing me.

Darryl Praill: So, a good sales kickoff process has to factor in all those aspects. You as a sales development professional and account executive or any kind of sales where you have, are dependent upon the other people. So, that’s a big part of what I’m doing and big part of the world we both collectively live in.

Darryl Praill: But the other part, when you’re at this time of the year, you actually have a chance to sit back and reflect a little bit, I don’t know about you but I do, because when we’re having all these conversations, there’s a couple of ways this can go. One is you’re like, “Yeah, high five, let’s go celebrate, “let’s hit the bar, whatever we’re here.” And there’s a lot of energy in the room. If this was 30 years ago, I’d say there’s a lot of testosterone in the room but thankfully things have changed.

Darryl Praill: So, there’s a lot of hype and energy and adrenaline and away we go. But the other thing you can do is you can say, “Listen, I see the assumptions, I see my revise quota, “and my revised comp plan and I don’t have faith. “You’ve made lots of promises to me “and I just don’t see it happening.” And now I’m starting to second guess my career; is this the career path that I want?

Darryl Praill: I trust myself, but I don’t feel like the company’s invested in me, I don’t feel like my leadership are being fair or reasonable or intuitive to what the market realities are. And I’m the one who’s having to answer why we didn’t hit quotas, or we didn’t make sales when I wasn’t equipped when the quotas were over, way too tall and so I’m bitter.

Darryl Praill: And that starts you to evaluate your career path, right? Is this the job for me? And maybe you’re all in in your career path or maybe you’re early and you’re going, “Is this what a normal sales role is like? “If this is the case, I don’t like it.” So, it’s that time of year, it’s highs and it’s lows, it’s expression and rah, rah, rah and it’s introspection. I had the same thing myself many years ago when I began my career, which was not at the time in sales.

Darryl Praill: Believe it or not, for those of you who don’t know, my true education, my formal education, is in computer science, I and my friends, believe it or not, despite my attitude and my spiky hair, I am a computer programmer by trade. If my marketing road collapsed on me today, I could theoretically go back and start coding tomorrow.

Darryl Praill: It’s like a trade. I could be a brick layer, a plumber, electrician, you may leave it, but you can always go back. And I did that for several years, but there came a point in my career, three, four years in, when I start to realize, this probably wasn’t the role for me long term from a variety of factors and I had to evaluate, “Am I in a dead end career?”

Darryl Praill: Now you’re sitting back at this point in time in 2020 going, “Oh my gosh, software engineers, “they make so much money and they are so in demand, are you stupid, Praill? Well, different time, different era and maybe yes, I was stupid. But we sit back, and you go, “Am I in the right career path?”

Darryl Praill: And that’s when I say to you, as it relates to Sales Development Roles, the SDR, the one thing I hear, fairly consistently is, is the Sales Development Role dead? Is it changing? Is this the right career path for me? I’m in SDR, I want to be an AE, but I’m not sure it’s ever going to happen, and I don’t feel like I’m encouraged, I don’t feel like I’m trained, I don’t feel like I’m given opportunity. They’d promise me stuff, it hasn’t happened. I don’t know what’s going on, I brought it up, nobody’s listening, what are my options?

Darryl Praill: Well my friend, you are not alone and it’s a legitimate question. So, guess what? It’s a hairy dicey, scary question that there is no correct answer, but there are a lot of opinions.

Welcome, Scott Ingram

Darryl Praill: So, we are going to bring in the one, the only, Scott Ingram to help us tackle this puppy and kind of educate and inform and give you some options for you to consider and evaluate, if you find yourself in this situation. Now, if you don’t know Scott, he is the founder of Sales Success Media, he is the host of Sales Success Stories and The Daily Sales Tips podcast, all of which you can find at his website, So top, T-O-P, the number 1,.fm. Now, of course I’m telling you all this and you’re all going, “We know who Ingram is, “get on with it Praill”. So, let’s just do exactly that. Scott, my friend, welcome to the show.

Scott Ingram: Darryl, thanks for having me. I’m super excited to dig into this conversation and really just dissect it a little bit. It’s something that’s been bugging me for a while, and I love that you provided the venue and the platform for us to hash this out a little bit.

Darryl Praill: Oh, I mean, and I’ll be honest with you, when this idea came up and I know we were talking about a couple ideas and this came up, I was jazzed because it is something that comes up and this is something that our audience does deal with. So, let’s get it out there, let’s give it some sunlight, let’s talk about it.

Darryl Praill: Why don’t we start with setting the stage, all right? Before we even get into how we found ourselves here. Talk to me a little bit about what you’re hearing from SDRs about the role, about the situation, about why we are even having this conversation, set the stage.

Scott Ingram: Sure, so this really started for me, I was having a conversation on my Sales Success Stories podcast, I only interview the best performers, right? They have to be active individual contributors and the either number one or top 1%. And I try and talk with a number of SDRs, right? We would talk to individuals across a variety of roles, but always try to include SDRs in those conversations.

Scott Ingram: And I was following up with one of those individuals who’s been on the show and we had this great discussion and he said, “You know, Scott, I feel stuck,” he said, “when I came into this organization, “they promised me after six months, “we’ll build a bridge for you “and we’ll set up a transition plan “so that you can move into the AE role that is your goal.”

Scott Ingram: And he’s been there much longer than six months, has nailed every single month that he’s been there. I mean, he’s absolutely crushing it. And he says to me, “Scott, there’s no bridge, “it just doesn’t exist. “And at the same time, recruiters call me all the time “and as soon as they find out “that I don’t have closing experience, “the conversation’s kind of over.” And this is a guy who’s doing great, right?

Scott Ingram: So, I think when you’re performing at very high levels, lots of doors open to you.What really worries me is what’s happening to the average SDR? I think too, we’re treating this role as a dime a dozen. Its entry-level. It’s churn and burn, we’re not serving the people that are serving us and helping us develop pipeline in our organizations. And I think that’s really, really wrong and we need to take a hard look at what is this really meant to be? And is it temporary? Is it a path?

Scott Ingram: Because I’m finding in, I’m going to say most here, I’m going to say the majority of organizations, it’s basically a dead end. There’s nowhere to go from that role in a good formalized way, you’re just kind of stuck. Now, there are some great organizations where they’re promoting people all the time and they’ve got a very good, well defined process, but there’s not enough of them.

What Role Does Organization Play in shaping up SDRs and AEs?

Darryl Praill:  So, it’s funny you say what you said. In 2019 VanillaSoft, I’ve shared this before, so regular listeners, I apologize. We recognize that our sales process was broken. Now, how do you recognize that? You recognize that because not enough reps are hitting their quota or they’re not happy with the commission. You have some churn, yada, yada. Okay, that’s setting the stage.

Darryl Praill:  So, we engaged experts to help us resolve this. And because we thought we were experts but if we we’re having this problem, maybe we need another outside voice. And one of the things we did, the one expert we brought in, they went through, exactly all the points you just made.

Darryl Praill: We talked about what’s the recruiting experience, blah, blah, blah? Before they actually sign the paperwork, you need to articulate to them what is their career progression from SDR to AE. Timelines, requirements, accomplishments and what’s the process if they achieve it and they don’t move forward.

Darryl Praill:  And so, what can they do? How are you going to review them? And measure them, give them that feedback. And then you need to give infrastructure to enable them to physically monitor this so they can see that they’re tracking against this goal, so they can get that career goal. And then that way when you tell them this in the interview, they’re going to be jazzed, because other employers, most employers don’t do this.

Darryl Praill:  And then big important part here, you actually have to do that. So, if you said, if you do this role for nine months or 12 months and you have to accomplish A, B, C, D and E, if you would do A, B, C, D and E, you damn well better make them an AE because that was the promise you made to them. Otherwise, you’re going to lose and then you just wasted all that money on training them and everything else, they’re gone to somebody else.

Darryl Praill:  So, that was a big thing we needed to do. We thought we had that, but we recognized we didn’t have our process formalized. So, I love hearing you say that, that they’re making, they’re being made promises and they think they’ve upheld their end of the deal, the sales rep and the organization themselves are not actually following through on their commitments to them. That’s got to be frustrating as hell.

Scott Ingram: Yeah, well, absolutely. And I think that, I want to look at this and talk about this from really two sides, right? So, what do organisations and sales leaders need to be thinking about as they’re building and developing and growing these teams? And on the flip side, what do the individuals like myself, I like to think of myself as an intentional individual contributor.

[bctt tweet=”So, what do organizations and #SalesLeaders need to be thinking about as they’re building and developing and growing these teams? 🎧 Listen as @ScottIngram explains. #SDRs #SalesManagement” username=”VanillaSoft”] 

Scott Ingram: So, if you are an SDR or you’re thinking about getting the sales and this is the path that you’re looking at, is that really the right thing or would you be better served by going into something that, again, if it’s entry level, it’s probably going to be a little bit more transactional. It’s probably a little bit more small business focused, but moving into a role that’s full cycle, where you’re going to get all of the experience and then move up from there. I think that’s an important way that you need to look at it for yourself, and just evaluate what’s the best fit for me? And where am I ultimately trying to get to? And what’s the best path?

Darryl Praill: All right, so let’s just break this down. So, folks listening normally go, “Hey Praill normally you talk about “what’s that 1% thing you can do different, “and that’ll make you marginally better “and are we getting there today?” Yes, we are going to get there. We’re going to offer solutions and options for you if you find yourself in this role. But to set the stage for that, we’ve got to understand the circumstances a little better.

Darryl Praill: So, we’re going to get a little bit big picture here. Scott, you talked, I’ve heard you talk about how leaders and companies need to prioritize career paths. So, what does that mean? So, if I’m in management listening to this episode, what are the things I should be doing? If I’m an SDR, what are the things I should be asking of my employer when it comes to prioritizing career paths?

Scott Ingram: Well, I think you articulated it pretty well. I mean the better job you can do on the front end to really define what that is. Here’s the trap though and here’s the trick and this is probably why this is so challenging for sales leaders. If I’m going to take somebody that was a strong good performing SDR and move them into that AE role when my other option is, I can hire somebody else that already has that AE experience, that experience gap is really significant.

Scott Ingram: The number of new skills that they’re going to need to learn and develop to be successful in that AE role is a lot. So, I think when we think about, it’s not the career path, yes. And the other part of that, that can be challenging is, is the organization growing enough that we’re going to be able to support enough people moving from the SDR ranks into that AE role? I think those are important conversations and you have to be honest with yourself and you have to be honest with your team in terms of how many of these types of opportunities exist.

Scott Ingram: It’s really about the development of that professional, yet we want them to be great SDRs. We want them to be converting better and creating more meetings and creating more opportunities, meaning being more efficient in their work as an SDR. But early on and throughout the process, and this may be an elongated process.

Scott Ingram: It might be a year or 18 months that you’re asking somebody to commit, before you move them to that role. But I think that also gives you the opportunity to then start to let them experience some of the other parts of the sales process and cross train with some of your other AEs so that they’re seeing all of the ins and outs of that full cycle.

Scott Ingram: I think the challenge in sales for so many people is, it’s kind of like a duck on water. There are so many things that are happening below the surface that you may not know or understand if you’re just looking at what’s happening above the water. And you’ve got to create opportunities for people to get some of that experience and some of that gain, some of that knowledge so that they’re going to make the transition well.

[bctt tweet=”I think the challenge in sales for so many people is, it’s kind of like a 🦆 duck on water…so many things are happening below the surface that you may not know or understand. ~ @ScottIngram #SalesTechnique #B2BSales” username=”VanillaSoft”]

Scott Ingram: Because the worst thing we want to do is have a great SDR, they performed well, they made that transition and then they thud as an AE. And now you’re in an even worse situation right now, you’ve got an open headcount, we’ve got to move that person on, it’s just a bad situation all the way down.

Scott Ingram: So, I think you’ve got to be very, very mindful of this entire process, very open about it, very transparent and communicating about what’s going on and what the realities are and what the realities of your business are.

Darryl Praill: All right, so we’ve talked a lot about the, you got to be mindful of this and is there a process in place which is on the onus of the employer and is the company growing, which is somewhat on the onus of the employer. But we haven’t talked about the actual part of it that is very personal, which is how do we contribute to this situation we find ourselves in?

Darryl Praill: And guess what, we’re going to go for a commercial so that you don’t go anywhere, and you’ll come back and you’re here. So, stay tuned, we’ll be right back. Okay, so I teased you just before we left here. I left you saying how do we own it. How do we address a situation?

Setting up the Right Sales Career Goals

Darryl Praill: Now to be clear in that, when I say we, I’m not talking about the big we, which is the entire sales community, our tribe. I’m really talking about you and me. How do we, how do I as an individual SDR own the situation I find myself in, which may be less than optimal and has me questioning if this is a career path for me and what can I do about it to try to remedy the situation? So, Scott, do you have any insights there you can share?

Scott Ingram: Yeah, I think I do. I think the first piece is just being intentional about it. This is a topic that I have spent a lot of time digging into. Last year at the Sales Success Summit that we host here in Austin, we spent an entire half-day and had a series of different panels talking about different career paths.

Scott Ingram: Whether you want to be an intentional individual contributor, or you want to move into leadership, or you want to go do something else. Maybe you want to start your own company, or you want to become an executive or you’re on that type of track. Until you understand where you’re trying to get to, you really can’t define what the appropriate steps are in between.

[bctt tweet=”Until you understand where you’re trying to get to, you really can’t define what the appropriate steps are in between. ~ @ScottIngram #B2BSales #SalesTips ” username=”VanillaSoft”]

Scott Ingram: So, at first, I think you have to take a look at the big picture and give some thought to what’s my ultimate goal here? Am I looking to move to an AE role? And if that’s the case, what is the best route? So, I’d say if you’re in an SDR role today, look at the realities of that situation. Look around you, look at your peers, are people being promoted? Does that path exist? Are you being given the opportunities to develop and grow these types of skills that are going to help you be successful as an AE?

Scott Ingram: And I think you’ve got probably three different paths to consider. One is, you work within your existing organization and you find that path and you execute on what they’re asking of you to do and you follow through and you move into that role. I think there’s, you may just recognize, “Yeah, you know what? “This isn’t the right place for me. “The current company doesn’t offer me “those types of opportunities and I’m not developing “and perhaps I need to make a change.”

Scott Ingram: And I think that the change, and this is where we get to the third piece, is do you move to another SDR role? Or do you look for what may feel like a little bit of a step down? Maybe you’re an enterprise SDR, you’re calling, you’re setting appointments with big companies, but to get that full cycle experience and to get that closing experience, maybe you need to move down market and into an SMB role and then kind of move back up.

Scott Ingram: It really comes down to where you want to be focused. Are you in the right industry? Again, there’s more considerations here than just kind of that SDR question. But asking yourself those questions, asking those questions of hopefully you’re developing some mentors and some folks who are further along in this journey than you are and getting their guidance and getting their advice and I suggest try not to go too far removed, right?

Scott Ingram: Don’t talk to somebody that did this 20 years ago. Talk to somebody that did this three years ago, five years ago, that has a little bit more recent relevant experience and maybe started as an SDR and it is that type of opportunity.

Scott Ingram: Then the last thing I’ll say is if you’re not yet into that role or again you are considering making that change, really looking at the whole of the organization that you’re looking to join and what they offer, right? Do they have a good reputation of training and developing people?

Scott Ingram: It’s interesting, I’ve had a number of conversations here recently and I spent some time in this industry, in kind of the payroll, HR solution space, so your ADPs, your paychecks, your TriNets, all of those types of organizations, traditionally offer great opportunities, great development, and it’s full cycle regardless of where you step in the organization. And I’ve seen a lot of people develop through those different organizations into enterprise SaaS sales and they’re fantastic at it. So, what’s going to serve you best and help you along your own career path and just being intentional about that.

The Skills to Invest in for Transition from SDR to AE

Darryl Praill: All right, so two more things I want to address on this whole what are my options discussion. One, we haven’t talked about this yet, what about me investing in me? In other words, I don’t have those skills, I don’t know how to close. Because as an SDR in my daily grind, I’m not closing.

Darryl Praill: So, maybe if I go and invest in, I read a whole bunch of books and go to some classes and sign up with Scott Ingram in his program or Mark Hunter or John Barrows or whomever and do some of that training and the company sees that I’m willing to invest in myself. Is that something that might get me into that AE role? Is that something I should be evaluating? I should be budgeting money in my take home to spend on me.

Scott Ingram: Yeah, it’s funny that you say that. Daily sales tip number two, I’m a year into that show, we’ve done a show every single day, so we’re over 365 episodes at this point. But the second tip, was one that I shared and it’s this idea of you have to own your own development. Nobody is ever going to care more or benefit more from the development that you do for yourself.

Scott Ingram: So, maybe your company has a great program, I’ve been talking with Google a lot. My God, they have so many different buckets of dollars available in so many different ways that they will help you develop yourself even outside of your professional life. But most organizations have something that you can tap into.

Scott Ingram: And again, I think that’s a good litmus test for whether or not this is the right organization, right? It’s are they going to allow me to go attend the sales success summit? Are they going to allow me to buy the books or have an Audible subscription? Are they’re going to allow me to have the time and the financial wherewithal to invest in some of this or at least a part of it, right?

Scott Ingram: But at the end of the day, I think it comes down to the individual, right? You can’t scapegoat your company on this and say, “Well they wouldn’t let me go to that training “or they wouldn’t give me the money for that.” You know what? Who does it matter to you the most?

Scott Ingram: I think that’s what it comes down to and one of the questions I have, and we’ll certainly be asking on LinkedIn here is how do you budget for that, right? What’s the right amount of investing in your own development? What portion should companies be contributing? But ultimately what should you be doing? Is it, I don’t know, 5% of your income? Is it 3%, is it 10%? Is that a percentage? Is it something else? I think this is a very, very valid question and something that you need to sort of define for yourself and then what’s the best place to go invest, not just the dollars, but your time, right? Where are you going to get the foundation that you need to take that next step and to really accelerate your career growth?

Darryl Praill: I love that it’s your daily sales tip number two, because last episode we talked about, we reviewed the top five episodes from the INSIDE Inside Sales podcast in 2019 and I picked five and the first one I picked on, it was a session I did with Andy Paul and it was called “Learn to Earn”. It was about investing in yourself. There are no excuses, you got to do that.

How to Approach your Employer for Help?

Darryl Praill: Okay, last thing I wanted to approach you on, we actually haven’t talked about this. What about just directly confronting, approaching my employer to say, “You promised, this hasn’t happened. “I am not happy, I might leave.” Now I’m giving you lots of examples. Should I approach them? And if so, how should I approach them?

Scott Ingram: Well, I would say no question, right? Why wouldn’t you do that, right? Again, it comes down to if you’re afraid of that or the organization’s not going to support that and you’re not getting that kind of leadership from your leader, you’re in the wrong place.

Scott Ingram: So, you should absolutely be having that conversation. It should be a regular part of your one-on-ones where you’re talking about your development and talking about your next steps. And I think there’s really two kinds of sales leaders, there are those who I love working for, that the best thing in their eyes that can happen is somebody grows beyond them and their career elevates them. That may mean that I leave that team and that they have to go fill that hole, but that’s what they value, those are the great sales leaders.

Scott Ingram: I think there’s another scarcity mindset of leaders and they probably don’t listen to podcasts, so, I don’t really have to worry about insulting any of them here. And that just is that, “Oh gosh, oh, I got to keep my team here, “I got to keep them down so that I don’t have those holes “to fill and I’m fully staffed “and I’ve got this consistent team.” I think that’s just, that’s really wrong.

Scott Ingram: So, you need to look at that space that you’re in, have those conversations, not just with your direct leader, but in other parts of the organization as well, where you’re looking to move to. Whose team might you be on at that point? Have a conversation with that sales leader, that sales manager, and get a good sense of what’s it going to take? What’s it going to take for me to develop the skills now to be successful on your team then, right? That’s what’s going to sort of smooth that runway and that path for you to be successful and to take that next step.

Darryl Praill: All right, so let’s kind of do a quick little dirty recap. Today, we talked about the untalkable, is my career dead? Have I chosen a path, am I with an employer that I simply cannot grow? And if I am, what the hell do I do? This is not a good situation. So, let’s recap just a few of the highlights that Scott shared with us.

Darryl Praill: When you’re in the interview process, you want to be aware if there’s a formal process that’s documented and supported, that’s going to move you from SDR to AE. Timelines, milestones, requirements, and is there infrastructure and reviews in place to physically make sure this communication stays open and expectations are managed both ways. That’s incumbent upon you in the interview process, all right?

Darryl Praill: Be smart, is the organization as you growing enough to support the number of AEs? Not everybody can be an AE, you may be qualified, they just may not have an opening and that’s not on you and that’s not on them, that’s just on the realities. Know what your ultimate goal is. Is it to become an AE? Or are you just assuming you want to be an AE? Maybe you want to be something else. So, if that’s the case, have a plan, what’s the best route, all right?

Darryl Praill: If you find yourself in this situation right now, what are your options? Well, you can just follow the process and adapt as to how they’re prescribed and wait it out. You can possibly move into another SDR role or you can actually move into a different market or role. Maybe if you’re enterprise, you go down to SMB.

Darryl Praill: So, those are some short-term requirements if you like your company and you want to stay with them. If you’re making a change, don’t repeat the mistake that you’re in now, so follow this advice. The other option is, you should continuously be investing in yourself. So, if you don’t have certain skills, “I don’t know how to close.” Spend money on you, you’re worth it. And by the way, you benefit because you’re the one that gets the bigger income because of those skills.

Darryl Praill: Finally, last solution, always talk to your employer. Keep those lines of communications open, make sure express your expectations, but key thing here, do it constructively, do not lash out, both sides want to win. So, with that, I don’t know if we’ve solved it for you folks, but we’ve certainly given you something to think about. Hopefully you are a 1% better today than you were when we started, when it comes to managing your career. Scott, what’s the best way to get a hold of you? Is it LinkedIn, is it Twitter, what is it?

Scott Ingram: LinkedIn or

Darryl Praill:, go there. Scott Ingram by the way, his podcasts are fantastic, right? So, if you’re not listening to his podcast, shame on you. If you’re to invest in yourself to learn, learn by following his podcast. But with that, we’re done, another week in the can. I had fun today, folks, I have to go back to my sales meetings. Thank you so much, Scott, and thank you folks. And that wraps another episode of INSIDE Inside Sales, we’ll talk to you soon, bye, bye.